Episode 106: Play Long Ball

In this episode Rob talks about “playing long ball”, thinking about as a founder or significant other of a founder, how to stay in this space for the long haul. He highlights three points to achieve this and goes into details on each.

Episode Transcript

Rob Walling:

So I needed an opener for the show, and I Googled “podcasting jokes,” and I guess the big joke is that most podcasts don’t have big audiences, or don’t have audiences at all. A bunch of the jokes are things like “What did the podcaster say to their audience? Is anybody out there?” And “what do you call a podcaster with an audience of one? Successful.” So while these jokes are not funny, it did make me thankful for you, our listeners. We have thousands of listeners every week, and we really appreciate you hanging around with us and sticking with us through these journeys.

We know that some of our shows are Sherry and I getting on the mic and talking about things we’re going through; other times it’s really instructional, educational, and then other times we’re interviewing successful people to find out what makes them tick and how they’ve done it in a sustainable fashion. This week, Sherry is on the road, and she’s actually dealing with multiple health issues in her family as well as doing a lot of one-on-ones at a conference on the West Coast, and so I’m flying solo, and I think it’s going to be awesome.

Rob Walling:

So this week, it’s just me, as I said in the intro. I’m going to be talking about playing longball, thinking about, as a founder or significant other of a founder, how to be in this game for the long term. I’ve picked three points that I want to talk about: the first one is valuing relationships over success. The reason that I find this so important is that I see founders who basically value their own success over the relationships around them, and they’re willing to either burn relationships or just burn people in general over this.

What I’ve learned over my 20 years, almost 20 years as an entrepreneur, is that you don’t become successful without relationships. It is such a monumental task to climb up this tower and reach the top and have some success as an entrepreneur, and at a certain point in my career, I thought that you could do it alone. I thought that I could accomplish this without anybody’s help, and the further that I’ve gone along, the more I’ve realized, there’s an old African proverb, it says “If you want to go fast, go alone; if you want to go far, go together.”

That’s how I think about this, is like, playing longball in entrepreneurship and not just coming in and trying to do something for one or two years because you want to make some money or you want to create your job. That’s not a sustainable approach to this. If you want to do it, value your relationships. And what I mean by that, there’s a number of things. I’m going to talk four of five different things that you can do to make sure that you’re valuing the people around you and you’re building relationships in a way where you’re not using people and where you’re not screwing them over.

So one thing is not to steal other people’s ideas. This is widespread, it’s insane how many times I’ve said something or written something or done something in a talk, and I will literally hear someone say it a couple weeks later in their own blog and act as if they came up with this, they stumbled upon this thing. This is stuff that I’ve been thinking about for years, I’ve been blogging about, very irritating. What’s funny is it doesn’t matter if someone, maybe if they quote you or if they use your idea, as long as they say “I heard this from this person.” Like, if you’re going to take other people’s ideas, give them credit.

I’m very, very careful about this. I try to be exceptionally careful. Whenever you hear me mention, fund-strapping is an example, which is a word coined by Colin from Customer.io. I use “fund-strapping all the time, and every time I say it, I reference back to him. When I talk about integration marketing, that’s a term that I coined, but I actually stole the idea from Ruben Gomez, and he’s well aware of that. If you watch any talks where I mention it, I say “Yeah, I stole this technique from Ruben Gomez.” Actually, I steal most of my good ideas from him, but I give him credit when I do that.

I’m not making this about me and how I do things, I’m saying in the long-term, the more people’s ideas you steal, the more people you’re going to piss off, because people notice. This is not some little secret world where we can hide off in our little cloisters and no one notices. We’re all in a pretty public space now, especially this small start-up ecosystem. So if you get a reputation for stealing others’ ideas, it isn’t cool.

Another thing is don’t burn relationships over petty things. If someone steals from you, someone screws you over, if someone is just dishonest, then all right, let’s talk about ending relationships or at least distancing yourself from that person so they don’t have influence on you. But I have had multiple conversations in the past couple years with founders, you know, we’re sitting trying to do kind of a business dealing, whether it’s, maybe it’s speaking at a conference or whether it’s some little business dealing. We’re all running seven-, some eight-figure [SaaS apps 00:04:54], so money, little amounts of money are not a big deal. People will push things to the point of anger over some $200 charge or a $200 something.

We’re having multiple phone conversations about this, and oftentimes I’m thinking to myself, “Are you (beep) kidding me that we’re sitting here having this conversation? You have wasted so much of all of our time; as founders, it’s extremely valuable. We’re running these big businesses with employees. Like, here, take the money.” I’ve gotten to the point where, if we start having conversations now about petty things, about small amounts of money, I will pull money out of my wallet and give it to people, because it’s a way of showing, like, “Don’t be petty. I thought our relationship was worth more than this $100 or $200.”

So the advice here is just to think, it’s not to let people push you over, it’s not to let people take money from you, but it’s to think before, think about the value of a relationship before you think about asking for something that, in the long term, it shows that you’re thinking short-term if you’re thinking about a $100 or a $200 thing. If you’re thinking long-term about relationships and what they’re actually going to yield you and what you can give to someone, it’s worth a heck of a lot more than that over the long term.

Continuing with this “valuing relationships over success,” you know, people aren’t dumb. Don’t bullshit them. You can get away with bullshitting someone a few times: you can talk someone into something, you can use your charisma, your influence or whatever to convince them of something, but people know what you’re doing. You hear about people with Steve Jobs, how he would bully them in or force them to do something and talk them into it; you can do that, that’s fine, if you have that power. But you hear about the people with Steve Jobs and they said “Yeah, and then later I regretted it. And then later I was pissed off at him. And then later I hated him.”

And it’s like, you know, what are we valuing here? Is you getting someone to do something worth more than the human relationship that you have with them? In the long term, if you are not Steve Jobs, if you are someone who is trying to build businesses and needs your reputation and you’re looking at being around for 10, 20, 30 years, and you didn’t start Apple and then come back to Apple and revitalize it, then you’re going to be in a precarious position. I have seen, I have a couple founders in mind right now who think that they are, they think they’re a little better than they are and they talk people into stuff and they pressure them, and then their reputation is severely tarnished.

I was actually talking to a friend of mine, a colleague, and it was funny, he brought this up and he said “Hey, do you know so-and-so and so-and-so?” And I was like, yes, and he says “Yeah, I really don’t like those guys.” I was like, “Wait, I thought that you were all kind of rolling in the same crew.” And he’s like, “No, these people, I feel like it’s transactional. I feel like they’re using me. I feel like they try to talk me into stuff. I feel like they try to pressure me into stuff.” And it’s like, man, I feel exactly the same way. This is why I’ve distanced myself from those people, because they’re always on the take, you know? It’s take-take; can you promote me, can you help me out, can you help me do this?

It’s a trip. It may seem like you’re getting away with it, but what you’ll notice is that people will distance themselves from you. You may not even notice that at the start, but in the long term, there’s only so many people doing this, it’s a pretty small world. People aren’t dumb; don’t bullshit them.

And the last point of this, I realize some of this has been a little negative, but I think I’m kind of fired up about this relationship thing, because I’m watching people think so short-term that they are burning relationships. They burn it with co-founders, they burn it with a colleague, they burn it with an employee, they burn with an investor, and I’m thinking, there’s almost never a reason to do that. People really sacrifice their relationships, and I think that if you’re thinking you’re going to do this, you’re going to be an entrepreneur, you’ve really got to stop and think about that.

The last point on this valuing-relationships is, decide who you’re going to go to the mat for, and then go to the mat for them when it counts. This is all about loyalty, right? It’s like, if you say that you’re going to back up your team, if you say you’re going to back up your co-founder, and then when it hits the fan, you basically make them clean up the mess or you kind of bail on them or you blame them, then you’re really going to piss people off, you know? I have memories of being on vacation and basically a toxic customer was bullying my team, as an example. And I go to the mat for my team, and nobody’s going to do that.

So I came in and it was just a shitshow, and this person was rude and it was not good. And I fired the customer, and it brought a lot of heat down on myself; it was just a big debacle. But I’m willing to do that for my team, because I’ve decided that I’m going to go to bat for them. I’m going to go to the mat for them, and I’m going to do that for my family, and I have certain friends, and in my mind, it’s pretty solid who I’m going to go to the mat for. When the time comes, I’m willing to sacrifice the time, anxiety, money, what it takes to really back them up. I think figuring that out in your own mind is something good to know, and hopefully you know that those people will go to the mat for you.

What I’ve found is the more that I’m willing to do that and the more I’ve shown that over time, the more that others are willing to back me up. That’s kind of this point, right, of valuing relationships over success, is that it’s not just that you’re giving, but that some of that giving comes back to you.

The second point I’m playing longball is to realize how little we all actually know. If you look in the start-up space, it’s becoming this, it’s kind of been this echo chamber for a while, but it’s getting even worse. I don’t know how many more Medium posts I can take from a 26-year-old kid who’s built a, maybe a six-figure business or maybe even he got lucky, he or she got lucky and built a seven-figure business, and they probably don’t actually know that much. They probably got a little lucky, they probably worked really hard, but then to trumpet that they’re an expert and they can teach everybody. They have this one success; one success doesn’t make you an expert.

Realize how little we all know. I am still someone who tries to humble myself when I’m around other people, and to figure out what are they better at than I am, right, and to do less talking and more asking of questions. Problem is, everyone claims they’re an expert these days. Everyone’s this teacher online: “Hey, I’ve done something once, now I’m going to teach that.” I find that that is actually not a good thing. I think in the greater start-up ecosystem, it’s been good that the world has become more transparent over the past 10 or 15 years, but I think the pendulum has swung too far, and my take on it is when I see, again, you know, someone who’s had single success trying to write a book or start these courses or claim that they’re an expert, the problem is that people believe them, and they can’t tell what’s the mirage and what’s not.

What’s funny is, after doing whatever you want to call it, six, eight, nine, 10 different businesses, it’s pretty obvious when I hear someone talking, it’s like, “Yeah, they think they know everything, but they actually are kind of two steps out of the crib, basically, and they can be an awesome founder, an awesome entrepreneur, but they need a few more years before they’re really going to know the mistakes that they could have made, what they stepped around, what actually made them successful, because when you’ve had one success, you just don’t know yet. You don’t know what you could have done wrong, and you can’t teach other people because they’re going to have different mistakes that you’ve never encountered. How can you guide them?

I guess what I’m saying here is, in realizing how little you know, is to take a posture of humility and don’t be the person who’s shouting at the top of your lungs about something that you’re so sure of that really you’re not actually sure of, because you’ve only done it once. I think the other thing that could be improved about the whole start-up ecosystem is people aren’t reading other people’s stuff and then saying “Oh, I want to build upon that. I want to stand on the shoulders of that person.” It comes back to giving credit.

I will see, over the course of these years, I’ve been blogging since 2005, so we’re talking 12 years. I’ve seen blog after blog, post after post, tweet after tweet, whatever it is, kind of saying the same thing, and it’s like, we get it. We get it, you ran these ads and this is how you built the business. Or you’ve had this realization of just “building a business is hard,” but it’s the same thing. We just saw that post from someone else six months ago, and so why are we rehashing the same stuff?

This is where people talk about it as an echo chamber, where it’s like, we’re all saying the same thing. Can we not get on with the fact that yes, most start-ups fail, and yes, it’s hard. Get to a next level where, like in academia, they actually move forward. They progress from the 1950s to today; people are quoting, giving credit, and then they’re building on the shoulders of giants. I would love to see the start-up space move in that direction, and the way to do that is for us to maybe be a little, each of us to be a little more humble.

If you’ve ever spoken with Dharmesh Shah, the co-founder of HubSpot, or with David Cancel, co-founder of Drift, or Jason Cohen, founder of WP Engine, these people are wildly, wildly, like, eight, nine figures-successful. Yet they’re always asking questions when you talk to them, they know that likely, you’re probably smarter, or at least more experienced in some area of your life. When I talk to them, they’re always asking me questions, even though they are wildly more successful than I am.

It was so funny, I was at a speaker dinner and Brian Balfour, who’s one of the best growth people in the world, in my opinion. He used to work for HubSpot, and now he’s running a start-up marketing school in the Bay Area. But we started talking and he starts asking me questions, and he’s like “Well, what do you think about this?” and genuinely listening for my opinion. Then he asked me “What books have you read recently that I’d be interested in?” It’s like, are you kidding me? This is awesome.

This is how I approach things, and it’s so cool to see that really successful people, not the ones who are kind of showing they’re successful online, but the people who I consider truly successful, are the ones who take a posture of learning and a posture of humility, and I think we could all learn something from that. I think that if you are playing longball and you want to be around the start-up space and help it become better, but also help yourself become better, realize how little you know and ask more questions, rather than claiming you’re the expert on something that you’ve done once.

The third and final piece of playing longball is to work at a sustainable pace. When I first started, I remember thinking that “Man, in X months I’m going to have something out, and I’m going to have a few grand a month in earnings from a product.” And I realized that you should think in years, not months, and then as soon as you get to the point where you have a little bit of money coming in, you should start to think in more like a decade or two than years.

The reason is that it’s pretty easy to burn yourself out, especially as you get older; you get into your thirties, you get into your forties and you have less energy, you can’t work at the same pace that you did when you were in your twenties, and so I think that focusing and working hard when you are working is extremely important. And then I think shutting it off when you’re not is extremely important.

I think that, to be honest, in the early days, and I go through seasons of this, but if you’re not working and you have a lot to do, then that time should be reserved for relationships, for time with your significant other, your kids. This may be controversial, but I actually believe you should turn off your hobbies in the early days of a start-up, or at least for a season here. I used to go through three- to six-month seasons, these windows of time where I would work a full day, then I’d make dinner, hang out with the kids, hang out with Sherry, and then I would start up again at 9:00 that night and work till midnight or 1:00.

That’s not sustainable forever, but it was sustainable for a few months here and there, and I got tremendous amounts of stuff done. I didn’t do it every night, but I did it maybe two, three nights a week, and that was the early days of growing HitTail, the early days of growing Drip, early days of Micropreneur Academy. These are the game-changing, it’s writing my book, these are the game-changing moments in my entrepreneurial career. What’s funny is they are actually, they’re non-sustainable periods of work, but I didn’t do them forever, which made them sustainable, if that makes sense.

You may have a slightly different working style, where you just want to work 40 hours a week. I don’t know if, that’s not how I work, and I don’t know if that’s something, if you’re going to actually get a start-up off the ground, doing that with a full-time job and aLl that. But you’re going to need to turn off the TV, and I would say shut your hobbies off for the time being, and then you can work-work-work for three months, and then you’ll start to feel like you’re doing too much, and then you can kind of step back.

Overall, I think this is maybe a bit more of a personal pace and a personal kind of work orientation that I’m making it out; I’m telling you how I did it, but the overarching theme here is work at a sustainable pace and think in terms of years when you’re thinking about your career. Maybe not a single start-up, right, you may not work on this single e-book you’re launching, or your little stair-step WordPress plug-in or your first SaaS app or whatever.

Maybe that’s not a decade-long thing, but if you want to be a founder, if you want to be an entrepreneur and you want to make this a living and do it for the rest of your life, which I think is amazing, I think it’s tremendous, I think it brings you freedom, I think it allows you to have purpose, and I think it allows you to have strong relationships. I think you should go for it, but think about these things: value your relationships over your success, because in the long run, relationships are what’s going to make or break your career, and realize how little you actually know, take this posture of humility, ask questions, and don’t claim to be the expert if you’re not.

And then work at a sustainable pace, figure out what that looks like for you and for your family, and I think that second part is pretty important, right? What will your significant other, what is he or she able to work with, how much time can you afford to spend with your kids and making that really, really good time, but then going back to work when it’s needed?

So I hope this has been helpful, kind of running solo here without Sherry, and I think the plan is next week for us to get back on the mic and continue doing kind of our normally scheduled programs. I’ve actually enjoyed the solo-Sherry episodes that she’s done over the past few months, when we’ve been in places where we can’t record, so hopefully this one comes off even half as good. Talk to you next week.

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Sherry has a unique combination of experience and education that results in an ability to completely understand what founders go through generally, crossed with their personal foibles specifically. The result is truly helpful, not regurgitated pop psychology or the “coaches” who haven’t been there before themselves.